RU99127449A - RECOVERY OF AROMATIC HALOGENIDES - Google Patents
RECOVERY OF AROMATIC HALOGENIDESInfo
- Publication number
- RU99127449A RU99127449A RU99127449/04A RU99127449A RU99127449A RU 99127449 A RU99127449 A RU 99127449A RU 99127449/04 A RU99127449/04 A RU 99127449/04A RU 99127449 A RU99127449 A RU 99127449A RU 99127449 A RU99127449 A RU 99127449A
- Authority
- RU
- Russia
- Prior art keywords
- oxygen
- tri
- mixture
- reducing agent
- reduced
- Prior art date
Links
- 238000011084 recovery Methods 0.000 title 1
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 239000001301 oxygen Substances 0.000 claims 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 9
- 239000003638 reducing agent Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- QENVUHCAYXAROT-RHSMWYFYSA-N Narwedine Natural products O1C(=C23)C(OC)=CC=C2CN(C)CC[C@@]23[C@H]1CC(=O)C=C2 QENVUHCAYXAROT-RHSMWYFYSA-N 0.000 claims 4
- 239000011261 inert gas Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N Nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
- 229910052786 argon Inorganic materials 0.000 claims 2
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910016469 AlC Inorganic materials 0.000 claims 1
- 229910010082 LiAlH Inorganic materials 0.000 claims 1
- JUNKBFQPKQYHKJ-UHFFFAOYSA-N [H-].[Na+].COCCO[AlH]OCCOC Chemical compound [H-].[Na+].COCCO[AlH]OCCOC JUNKBFQPKQYHKJ-UHFFFAOYSA-N 0.000 claims 1
- QTLCZDJAKCIBDO-UHFFFAOYSA-N [K+].CCCCC[BH-](CCCCC)CCCCC Chemical compound [K+].CCCCC[BH-](CCCCC)CCCCC QTLCZDJAKCIBDO-UHFFFAOYSA-N 0.000 claims 1
- MPNLMVOOQKZMDW-UHFFFAOYSA-N [Li+].CCCCC[BH-](CCCCC)CCCCC Chemical compound [Li+].CCCCC[BH-](CCCCC)CCCCC MPNLMVOOQKZMDW-UHFFFAOYSA-N 0.000 claims 1
- XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical compound [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 claims 1
- -1 aromatic halides Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000011363 dried mixture Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 239000001307 helium Substances 0.000 claims 1
- 229910052734 helium Inorganic materials 0.000 claims 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium(0) Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- ACJKNTZKEFMEAK-UHFFFAOYSA-N lithium;tri(butan-2-yl)boranuide Chemical compound [Li+].CCC(C)[BH-](C(C)CC)C(C)CC ACJKNTZKEFMEAK-UHFFFAOYSA-N 0.000 claims 1
- AMCNGINELBODDW-UHFFFAOYSA-N lithium;triethylboron(1-) Chemical compound [Li+].CC[B-](CC)CC AMCNGINELBODDW-UHFFFAOYSA-N 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 1
- 230000001681 protective Effects 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- ALDKXMLLZDHWRZ-UHFFFAOYSA-N sodium bis(2-methoxyethoxy)aluminum hydride Substances [H-].[Na].COCCO[Al+]OCCOC ALDKXMLLZDHWRZ-UHFFFAOYSA-N 0.000 claims 1
- XJIQVZMZXHEYOY-UHFFFAOYSA-N sodium;bis(2-methoxyethoxy)alumanuide Chemical compound [Na+].COCCO[AlH2-]OCCOC XJIQVZMZXHEYOY-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Claims (11)
Аr-Хn
где Аr - ароматический остаток, в случае необходимости одно- или многократно замещенный, в случае необходимости аннулированный и в случае необходимости, содержащий один или более гетероатомов (О, S, N), Х обозначает фтор, хлор, бром и/или йод и n равен от 1 до 10, с помощью гидрирующего реагента в качестве восстановителя в присутствии кислорода до соединения общей формулы (II)
Аr-Хn
где Аr и n имеют вышеуказанные в формуле (I) значения, отличающийся тем, что в качестве восстановителя используют диизобутилалюминийгидрид, диизобутилалюминийгидрид/ZnСl2, алюминийизопропилат, гидрид натрий бис(2-метокси-этокси)-алюминийгидрид, три-втор.-бутилборгидрид калия, три-втор.-бутилборгидрид лития, трисамилборгидрид калия, трисамилборгидрид лития, Li-три-трет-бутокси-АlН, Li-три-этокси-AlH, 9-(боробицикло(3.3.1)нонан, триэтилборгидрид лития, АlН3•АlС2Н или комбинация по меньшей мере двух вышеназванных восстановителей, при этом восстановление проводят в растворителе в отсутствие влаги, и что через реакционную смесь продувают или просасывают кислород в виде высушенной смеси кислорода и инертного газа.1. A method for reducing aromatic halides of general formula (I)
Ar-x n
where Ar is an aromatic residue, if necessary, once - or repeatedly substituted, if necessary canceled and, if necessary, containing one or more heteroatoms (O, S, N), X denotes fluorine, chlorine, bromine and / or iodine and n equal from 1 to 10, using a hydrogenating reagent as a reducing agent in the presence of oxygen to a compound of the general formula (II)
Ar-x n
where Ar and n have the above values in the formula (I), characterized in that diisobutyl aluminum hydride, diisobutyl aluminum hydride / ZnCl 2 , aluminum isopropylate, sodium bis (2-methoxy-ethoxy) -aluminium hydride, tri-sec.-butyl hydrohydride-sodium, hydride sodium bis (2-methoxy-ethoxy) -aluminium hydride, tri-sec. , lithium tri-sec-butylborohydride, potassium trisamylborohydride, lithium trisamylborohydride, Li-tri-tert-butoxy-AlH, Li-tri-ethoxy-AlH, 9- (borobicyclo (3.3.1) nonane, lithium triethylborohydride, AlH 3 • AlC 2 H or a combination of at least two of the above-mentioned reducing agents, while reducing This is carried out in a solvent in the absence of moisture, and that oxygen is blown through or drained through the reaction mixture in the form of a dried mixture of oxygen and inert gas.
12. Способ получения нарведина, отличающийся тем, что бромнарведин, в частности, бромформилнарвединкеталь восстанавливают восстановителем, , в частности, восстановителем по пп.1 и 2 в отсутствие кислорода до бромнарведина, в частности, бромнарвединкеталя, и последний восстанавливают восстановителем по пп.1 и 2 в присутствии кислорода до нарведина, в частности, нарвединкеталя, при этом отщепляется только присутствующая защитная кетальная группа.11. The method according to p. 10, characterized in that restore bromnarvedine-propylene glycol ketal formula
12. A method of producing narvedin, characterized in that bromnarvedine, in particular, bromoformalnarvedinketal, is reduced by reducing agent, in particular, by reducing agent according to claims 1 and 2, in the absence of oxygen, to bromnarvedine, in particular, bromnarvedineketal, and the latter is reduced by reducing agent according to claims 1 and 2, in the presence of oxygen to narwedine, in particular, narvedineketal, only the present protective ketal group is split off.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT?865/97 | 1997-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU99127449A true RU99127449A (en) | 2001-09-10 |
Family
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